Windshield Wiper Over An Airplane's Curved Windshield
You can try bend Wiper by curve object and curve object shrinkwrap on Glass.
It depence on what wiper vertices you want to bend you can limited it by Vertex Group.

Quick example is not perfect &quot;wiper&quot; rotates on its Z axis. I will have to check it later.

Or Bendi Bones could work in similar way as well.

Add-on Wiper
for 2.79 (Luca Rood) https://gumroad.com/l/wiper